#------------------------------------------------------------------------------
#$Date: 2008-04-05 09:13:02 +0100 (Sat, 05 Apr 2008) $
#$Revision: 340 $
#$URL: svn://www.crystallography.net/cod/cif/2/2100847.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2100847
loop_
_publ_author_name
'Ianelli, S.'
'Nardelli, M.'
'Belletti, D.'
'Jamart-Gr\'egoire, B.'
'Mouaddib, A.'
'Caub\`ere, P.'
_publ_section_title
;
 Synthesis and structure of new bronchospasmolytic agents. II
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              687
_journal_page_last               695
_journal_volume                  48
_journal_year                    1992
_chemical_formula_moiety         'C21 H29 N O4'
_chemical_formula_sum            'C21 H29 N O4'
_chemical_formula_weight         359.5
_chemical_name_systematic
;
      1-hydroxy-3-(2'-methyl-1',3'-dioxolan)-8-morpholino-tricyclo
      [6.5.0.02,7]trideca-2,4,6-triene          (compound 4)
;
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_cell_angle_alpha                90
_cell_angle_beta                 99.10(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.77(2)
_cell_length_b                   6.8810(10)
_cell_length_c                   17.867(10)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293
_cell_measurement_theta_max      19
_cell_measurement_theta_min      10
_cell_volume                     3735(4)
_computing_cell_refinement       'LQPARM (Nardelli & Mangia)'
_computing_data_reduction        'DIFAU (Ugozzoli et al.)'
_computing_molecular_graphics    'ORTEP (Johnson)'
_computing_structure_refinement  'SHELX76 (Sheldrick)'
_computing_structure_solution    'SHELX86 (Sheldrick)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       Siemens-AED
_diffrn_measurement_method       theta-2theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'standard Molybdenum anode'
_diffrn_radiation_type           'Xray MoKalpha mean'
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3292
_diffrn_reflns_reduction_process
;
   Only one quadrant of data (an asymmetric set) was measured
;
_diffrn_reflns_theta_max         25
_diffrn_reflns_theta_min         3
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    .0819
_exptl_absorpt_correction_type   'not applied'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_description
;
?
;
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.13
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     'not applied'
_refine_ls_goodness_of_fit_obs   2.4859
_refine_ls_hydrogen_treatment    'not refined'
_refine_ls_matrix_type           'full matrix'
_refine_ls_number_constraints    0
_refine_ls_number_parameters     351
_refine_ls_number_reflns         1575
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.0392
_refine_ls_shift/esd_max         0.04
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      'unit weights'
_refine_ls_wR_factor_obs         0.0457
_reflns_number_observed          1575
_reflns_number_total             3292
_reflns_observed_criterion       2.0sigma(I)
_[local]_cod_data_source_file    ge0307.cif
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-10 4 8
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
N Nitrogen .004 .003 'IT.4 Tab. 2.2A 2.3.1'
O Oxygen .008 .006 'IT.4 Tab. 2.2A 2.3.1'
C Carbon .002 .002 'IT.4 Tab. 2.2A 2.3.1'
H Hydrogen .000 .000 'IT.4 Tab. 2.2C'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_calc_attached_atom
_atom_site_type_symbol
N -.44080(10) .0428(5) -.1195(2) .0343(12) Uani . . N
O1 -.37550(10) .2217(4) -.1689(2) .0513(12) Uani . . O
O2 -.51370(10) .2387(5) -.0719(2) .0561(12) Uani . . O
C1 -.37840(10) -.1032(6) -.2286(2) .0282(12) Uani . . C
C2 -.36820(10) -.1377(6) -.3011(2) .0310(13) Uani . . C
C3 -.39270(10) -.2847(7) -.3415(2) .0395(15) Uani . . C
C4 -.42460(10) -.3902(7) -.3116(2) .0418(15) Uani . . C
C5 -.43440(10) -.3529(7) -.2395(2) .0398(15) Uani . . C
C6 -.41070(10) -.2047(6) -.1996(2) .0303(14) Uani . . C
C7 -.40440(10) -.0951(6) -.1242(2) .0312(15) Uani . . C
C8 -.36560(10) .0207(6) -.1577(2) .0346(14) Uani . . C
C9 -.31870(10) .0031(8) -.1161(2) .0507(19) Uani . . C
C10 -.29860(10) -.1986(10) -.1093(3) .063(2) Uani . . C
C11 -.3112(2) -.3219(9) -.0452(3) .062(2) Uani . . C
C12 -.3596(2) -.3821(7) -.0545(2) .0515(17) Uani . . C
C13 -.39190(10) -.2149(7) -.0522(2) .0379(14) Uani . . C
C14 -.48530(10) -.0409(7) -.1334(2) .0449(16) Uani . . C
C15 -.5186(2) .1222(8) -.1390(3) .0569(19) Uani . . C
C16 -.4701(2) .3150(7) -.0554(3) .0530(18) Uani . . C
C17 -.43580(10) .1541(7) -.0478(2) .0431(16) Uani . . C
O3 -.32720(10) -.0942(5) -.40490(10) .0473(10) Uani . . O
O4 -.29280(9) -.0307(5) -.2857(2) .0499(12) Uani . . O
C18 -.2897(2) -.2178(9) -.3918(3) .068(2) Uani . . C
C19 -.2698(2) -.1857(10) -.3118(3) .083(3) Uani . . C
C20 -.33420(10) -.0168(7) -.3334(2) .0386(15) Uani . . C
C21 -.3468(2) .1937(7) -.3428(3) .0524(19) Uani . . C
H1O -.4038 .2320 -.1735 .08 Uiso calc O1 H
H3 -.3870 -.3177 -.3979 .08 Uiso calc C3 H
H4 -.4424 -.5024 -.3451 .08 Uiso calc C4 H
H5 -.4582 -.4363 -.2159 .08 Uiso calc C5 H
H91 -.2986 .0974 -.1468 .08 Uiso calc C9 H
H92 -.3179 .0632 -.0606 .08 Uiso calc C9 H
H101 -.3087 -.2754 -.1623 .08 Uiso calc C10 H
H102 -.2630 -.1854 -.1016 .08 Uiso calc C10 H
H111 -.2916 -.4496 -.0366 .08 Uiso calc C11 H
H112 -.3053 -.2354 .0072 .08 Uiso calc C11 H
H121 -.3662 -.4511 -.1091 .08 Uiso calc C12 H
H122 -.3630 -.4846 -.0112 .08 Uiso calc C12 H
H131 -.3795 -.1163 -.0075 .08 Uiso calc C13 H
H132 -.4226 -.2765 -.0390 .08 Uiso calc C13 H
H141 -.4896 -.1359 -.0876 .08 Uiso calc C14 H
H142 -.4896 -.1210 -.1854 .08 Uiso calc C14 H
H151 -.5138 .2152 -.1854 .08 Uiso calc C15 H
H152 -.5507 .0634 -.1480 .08 Uiso calc C15 H
H161 -.4646 .4106 -.1005 .08 Uiso calc C16 H
H162 -.4669 .3951 -.0034 .08 Uiso calc C16 H
H171 -.4034 .2175 -.0368 .08 Uiso calc C17 H
H172 -.4402 .0602 -.0018 .08 Uiso calc C17 H
H181 -.2662 -.1663 -.4292 .08 Uiso calc C18 H
H182 -.2976 -.3616 -.4050 .08 Uiso calc C18 H
H191 -.2733 -.3180 -.2793 .08 Uiso calc C19 H
H192 -.2347 -.1548 -.3055 .08 Uiso calc C19 H
H211 -.3775 .2036 -.3803 .08 Uiso calc C21 H
H212 -.3229 .2785 -.3659 .08 Uiso calc C21 H
H213 -.3504 .2514 -.2886 .08 Uiso calc C21 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N .0342(19) .038(2) .0312(18) -.0035(17) .0081(14) -.0010(18)
O1 .087(2) .0255(17) .0492(19) -.0044(16) .0333(17) -.0081(17)
O2 .048(2) .063(3) .061(2) -.0042(19) .0194(16) .0115(19)
C1 .029(2) .027(2) .028(2) -.0015(18) .0005(16) .0014(19)
C2 .035(2) .031(2) .026(2) .0003(19) .0016(17) .007(2)
C3 .045(3) .041(3) .031(2) -.008(2) -.0002(19) .008(2)
C4 .048(3) .035(3) .038(2) -.008(2) -.005(2) -.003(2)
C5 .044(3) .038(3) .035(2) -.001(2) -.0003(19) -.006(2)
C6 .031(2) .029(2) .030(2) -.0016(19) -.0007(17) .002(2)
C7 .030(2) .036(3) .028(2) -.0019(19) .0069(16) -.003(2)
C8 .036(2) .039(3) .030(2) -.004(2) .0086(18) -.009(2)
C9 .039(3) .077(4) .035(2) -.009(3) .0030(19) -.024(3)
C10 .036(3) .109(5) .043(3) .001(3) .001(2) .017(3)
C11 .054(3) .090(5) .040(3) .003(3) .000(2) .025(3)
C12 .063(3) .048(3) .040(3) -.000(3) -.003(2) .009(3)
C13 .042(3) .040(3) .030(2) .000(2) .0027(18) -.000(2)
C14 .033(2) .051(3) .049(3) -.007(2) .0042(19) -.001(2)
C15 .042(3) .064(4) .065(3) -.002(3) .006(2) .005(3)
C16 .063(3) .045(3) .054(3) -.006(3) .019(2) .005(3)
C17 .048(3) .047(3) .035(2) -.008(2) .010(2) .000(2)
O3 .0537(19) .061(2) .0300(15) -.0031(16) .0144(13) .0132(18)
O4 .0348(16) .075(3) .0402(16) -.0085(18) .0056(13) .0031(18)
C18 .063(3) .079(4) .065(3) -.015(3) .016(3) .022(3)
C19 .075(4) .112(6) .062(4) -.009(4) .007(3) .049(4)
C20 .042(2) .047(3) .028(2) -.005(2) .0068(18) .006(2)
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
N O1 2.626(5)
N O2 2.859(5)
N C6 2.495(5)
N C8 2.518(5)
N C13 2.505(5)
N C15 2.428(5)
N C16 2.441(6)
O1 C1 2.472(4)
O1 C7 2.532(5)
O1 C9 2.385(5)
O2 C14 2.444(5)
O2 C17 2.438(5)
C1 C3 2.354(5)
C1 C4 2.730(5)
C1 C5 2.420(5)
C1 C7 2.144(5)
C1 C9 2.604(5)
C1 C20 2.553(6)
C2 C4 2.443(6)
C2 C5 2.876(6)
C2 C6 2.442(5)
C2 C8 2.774(5)
C2 O3 2.421(5)
C2 O4 2.407(5)
C2 C21 2.519(6)
C3 C5 2.436(6)
C3 C6 2.735(5)
C3 O3 2.790(5)
C3 C20 2.564(6)
C4 C6 2.354(5)
C5 C7 2.764(5)
C6 C8 2.138(5)
C6 C13 2.608(5)
C6 C14 2.967(6)
C7 C9 2.705(6)
C7 C12 2.609(6)
C7 C14 2.498(5)
C7 C17 2.480(6)
C8 C10 2.590(6)
C8 C13 2.706(6)
C9 C11 2.563(7)
C10 C12 2.580(7)
C11 C13 2.576(6)
C13 C17 2.882(6)
C14 C16 2.820(6)
C14 C17 2.393(6)
C15 C16 2.348(6)
C15 C17 2.809(6)
O3 O4 2.265(4)
O3 C19 2.314(6)
O3 C21 2.394(5)
O4 C18 2.306(6)
O4 C21 2.376(5)
C18 C20 2.307(7)
C19 C20 2.278(7)